The 5 Biggest Challenges in the YouEconomy and How to Face Them

Congratulations, you’ve escaped the 9-5 to become a solopreneur! You’ve decided to join the YouEconomy, that growing global movement of pioneers who have opted out of being told what to work on, for how many hours, by a boss who also wonders who set up this antiquated, industrial, consumption-obsessed economy.

Will you write cheeky marketing copy for clients on Freelancer.com? Put your graphic design talents to work on Fiverr? Maybe it’s your own online business selling ‘80s video game memorabilia.

Lego Despair

After backpacking Africa for seven months, how could I go back to work in government? Instead, I decided to create carbon neutral homes with better insulation, solar panels; all the green stuff.

My mom was thrilled that I moved into her basement. For two weeks, I was ultra-productive, writing a business plan, connecting with builders and working on a company logo. But as weeks passed, I spent more time below ground playing Fallout 3, procrastinating and ignoring my vicious mental chatter.

On a Friday morning, I found my old Lego train set and thought it would be pleasantly nostalgic to snap it together. I finished, stood back and… despaired. I was 26, but I felt like a 10-year-old. What was I doing with my life?

I was out of money, living in my mom’s basement and saw no hope for my business. Terror set in. Back to government I went.

Fantastic Self-Doubts and Where to Find Them

It took me five tries, four businesses and 10 years to escape into the YouEconomy. I’ve become familiar with every form of self-doubt and have learned how to get out of my own way.

Here are the five biggest challenges to making it on your own and how to face them:

1. Self-Motivation

“The best motivation is self-motivation. The guy says, ‘I wish someone would come by and turn me on.’ What if they don’t show up? You’ve got to have a better plan for your life.” —Jim Rohn

Those entering this new world for the first time won’t understand the challenge of self-motivating. From the day we’re born, we’re told what to do and when. In kindergarten, “Now it’s time to paint.” Catch the bus at 8 a.m. Take this test, and graduate. Go to college and take the required courses. Then, go straight into your first job and work defined hours, on specific tasks handed down from on high.

When you become your own boss, the first question is, “What do I do now?” Look around, and for the first time in your life, there’s nobody there to tell you.

You’re now the CEO of a corporation of one. Not only are you responsible for setting a strategy, finding clients and managing cash flow, you’ve also got to keep the entire company motivated and morale high.

How to face it:

Losing your motivation (easily and often) in the YouEconomy is a guarantee. The best way to keep moving forward is to create a vivid and emotional mental picture of your why and conjure it daily. It may be adequate to fire yourself up about how unhappy you were in your old job and how much you never want to go back.

I’d recommend creating a positive picture, a clear one that includes how you’re using your freedom, who you’re serving, the stupid amounts of money you’re making and what it allows you to do. Then, whip yourself into an emotional tornado until your desire for that life is a 10 out of 10.

Put on pants, daily.

2. MoneyPanics

“Worrying is praying for stuff you don’t want.” —Jen Sincero

The day you quit your job will be pure happiness and excitement. Your first MoneyPanic will come visit when you look at your bank account three weeks later and project forward how many months of food and rent you have left.

If you’re not adept at controlling your mind, this state of panic can become a default anxiety, always on your shoulder. It will virtually impair your ability to do good work and make smart decisions.

How to face it:

Before you jump ship at your old job, write down the dollar amount you need to survive, monthly. Decide how many months of runway you’ll need to replace your income. Then, double it (expect the unexpected). Save that amount before you quit.

Ensure you have some consulting work that can help pay the bills (even if consulting is a few bartending shifts per week). During my last 9-5 job, I secured consistent work in the gig economy that paid my rent, and then some. It gave me the security I needed to give those MoneyPanics the boot.

3. I’m Not Good Enough

“Most people overestimate what they’re going to do in a year, and they underestimate what they can do in a decade or two or three or four.”—Tony Robbins

At the start of trying to make it in the YouEconomy, you’ll probably be terrible at whatever you choose to do. Do you remember how long it took you to feel confident in your current role? Now, imagine starting a new job plus trying to do every other job in the company—bookkeeping, sales and marketing, web and graphic design, video editing, customer support—all while trying to be the CEO of your one-person enterprise.

Leaving a job that you’re good at to pursue several new roles, rolled up into one, it becomes easy to start questioning your worth as a human.

How to face it:

De-link your worth as a person from your productivity or success. I still struggle with this, but remind myself: Do you love your nieces and nephews any less because they aren’t yet good at things? Would you love your wife less if she was in a car accident and spent six months in the hospital, unable to work? Why love myself any less when I struggle?

Grow your patience muscle. “Dealing with the temporary frustration of not making progress is an integral part of the path towards excellence,” says world-renowned coach Christopher Sommer. “Quality long-term results require quality long-term focus. No emotion. No drama. No beating yourself up over small bumps in the road. Learn to enjoy and appreciate the process.” Show up. Do the work. Results will follow, but on their own timelines.

4. I Need to Push Myself Harder

“Ours is a culture where we wear our ability to get by on very little sleep as a kind of badge of honor that symbolizes work ethic, or toughness, or some other virtue—but really, it’s a total profound failure of priorities and of self-respect.”—Maria Popova

Early in my journey into solopreneurship, I chose a new computer desktop background, an image of one of the D-Day landings in 1945, shot from the boats, soldiers storming the beach and taking fire. The caption above was, “Harden the F*** Up.” I thought that this constant kick in the pants would help. If I wanted to make it, I’d need to toughen up.

Forcing myself to live under this guillotine only created depression and anxiety, feelings of worthlessness, disdain for my work and led me into burnout. I didn’t need to harden up; I needed to balance! When you go to the gym, you work near your limits, not so hard that you pull a ligament. Throttle down.

How to face it:

Protect your most important asset: you. If you owned a factory, you wouldn’t whip your employees; you’d praise them. You wouldn’t kick the machines to work faster; you’d maintain them regularly. When your mental and emotional states are balanced and healthy, you do your best work. Creativity flows and your relationships improve, which are all-important in any business.

Leave something in the tank. This actually makes you more productive. Hemingway would stop writing when he was in the middle of a flowing thought or a scene so that he would have an appealing place to start the next day (and would be drinking wine by noon). He knew to stop before the writing became a chore.

5. Not Having an Off Button

“To every thing there is a season, and a time to every purpose under the heaven.”—Ecclesiastes 3:1-8

As your own boss, you’ll be tempted to work in every waking moment. Early in my journey, my “official” working hours were 8 a.m. to around 6 p.m. However, I’d find myself responding to email, making minor tweaks to my website and reading marketing blogs into the night, all while watching TV.

This “half-there” work is counterproductive on two counts. First, anything you do while multitasking is lower quality. Second, you need absolute downtime—to unplug—to keep yourself sharp and do great work.

How to face it:

Schedule downtime. There’s a time for work and a time for effort. Use the “unschedule” to protect time for play, exercise, friends and inactivity.

Take a tech vacation. Put your phone in a drawer and power down your laptop. If you’re not disciplined enough to stay away, use apps to block your access to certain sites, apps or the internet. I’ve heard good things about Freedom.

Lastly, remember why you’re working in the YouEconomy in the first place: to set your own schedule and work on what you want, when you want; to love your life and to feel joy and happiness most of the time. Blow off work once in a while to enjoy your freedom and you might just find your footing here in the new world.